US20110274727A1 - Depigmenting topical compositions and their uses - Google Patents

Depigmenting topical compositions and their uses Download PDF

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Publication number
US20110274727A1
US20110274727A1 US13/126,215 US200913126215A US2011274727A1 US 20110274727 A1 US20110274727 A1 US 20110274727A1 US 200913126215 A US200913126215 A US 200913126215A US 2011274727 A1 US2011274727 A1 US 2011274727A1
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United States
Prior art keywords
composition
rucinol
weight
salts
respect
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
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US13/126,215
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English (en)
Inventor
Philippe Andres
Isabelle Pelisson
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Galderma Research and Development SNC
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Galderma Research and Development SNC
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Priority to US13/126,215 priority Critical patent/US20110274727A1/en
Assigned to GALDERMA RESEARCH & DEVELOPMENT reassignment GALDERMA RESEARCH & DEVELOPMENT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PELISSON, ISABELLE, ANDRES, PHILIPPE
Publication of US20110274727A1 publication Critical patent/US20110274727A1/en
Abandoned legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • the present invention relates to the use of rucinol or one of its salts, as sole pharmaceutical active principle, at a concentration of 3 to 10% by weight, preferably of 3 to 5% by weight and more preferably of 5% by weight, with respect to the total weight of the composition, in a topical composition, the said composition being intended for the treatment of hyperpigmentary disorders of the human skin.
  • Hyperpigmentation of the skin is a common disorder expressed by the appearance of liver spots or coloured blemishes on skin fragments. Hyperpigmentation occurs during accumulations of melanin in the skin, conferring nonuniformity on the skin.
  • the pigmented patches can appear on any part of the body, in particular on the backs of the hands, the face, the neckline and bald heads.
  • a common form of hyperpigmentation among disorders of pigmentation consists of age spots or sun spots. They are due to damage from the sun and usually appear on the backs of the hands and arms, on the neckline or on the face. These spots are darker than freckles or ephelides, and persist into the winter.
  • Chloasma or melasma patches are more extensive than age spots and are localized on the face. They are often but not solely related to hormonal changes. Pregnancy, for example, can trigger the excess production of melanin, which causes the “mask of pregnancy”.
  • the changes in colour of the skin can result from external causes, such as, for example, skin diseases, such as acne, or skin lesions.
  • Freckles are also small brown spots which can appear anywhere on the body but are commonest on the face and arms. Freckles are often an inherited characteristic.
  • Postinflammatory hyperpigmentation is also a frequent disorder of pigmentation which results from various cutaneous disorders and also from therapeutic interventions. This excess in colouring of the skin can be attributed to infections, allergic reactions, mechanical injuries, such as an abrasion or a scar, reactions to medicaments, such as tetracycline, bleomycin, doxorubicin, 5-fluorouracil, busulfan, arsenic compounds, silver, gold, antimalarial medicaments, hormones and clofazimine, phototoxic eruptions, a scar, a trauma, such as a burn, and also the consequence of inflammatory diseases, such as acne, lichen planus, lupus erythematosus, atopic dermatitis and cutaneous T cell lymphoma.
  • medicaments such as tetracycline, bleomycin, doxorubicin, 5-fluorouracil, busulfan, arsenic compounds, silver, gold, antimalarial medicaments, hormones and clofazimine,
  • PHIP is commoner in dark phototypes, such as noncaucasian skin, in particular Asian, black or mixed race skin.
  • depigmenting agents or lightening agents currently used in the form of topical compositions make it possible to reduce the density of melanin in the epidermis and possibly in the dermis. These agents are generally absorbed through the lower layers of the epidermis and slow down the formation of melanin.
  • Hydroquinone is a depigmenting agent, as are its derivatives, such as benzyloxyphenol and hydroquinone monobenzyl ether. Hydroquinone is the reference depigmenting product conventionally used for more than 30 years worldwide for the treatment of hyperpigmentary disorders, such as melasma or lentigines. This depigmenting agent is used mainly at 2 or 4%, depending on the country, in creams, gels or lotions and is applied twice daily, in the morning and in the evening.
  • hydroquinone is unstable in an alkaline medium and is oxidized in the form of quinone, which gives a brownish colour to the compositions comprising it; moreover, hydroquinone is irritating; it can also induce hypersensitivity reactions and, in some rare cases, ochronosis (disorder of the colouring of the skin, characterized by the appearance of blue-black blemishes); hydroquinone is also suspected of being carcinogenic; hydroquinone monobenzyl ether is not correctly metabolized when it is absorbed through the skin and brings about irreversible depigmentations.
  • Methoxyphenol a hydroquinone ether, which exhibits the disadvantage of being not very soluble in water and difficult to incorporate in cosmetic or dermatological formulations, is also known.
  • a depigmenting composition comprising hydroquinone, retinoic acid and dexamethasone has been described (U.S. Pat. No. 3,856,934) but this composition is also irritating and can, in the most extreme cases, bring about itching sensations.
  • a problem which the invention intends to solve is that of producing a composition which shows an improved effectiveness in the dermatological treatment of pigmentation, without the disadvantages of the compositions of the prior art.
  • a first subject-matter of the invention is a topical composition intended for the treatment of disorders of pigmentation of the skin, characterized in that it comprises, in a physiologically acceptable medium, rucinol or one of its salts, as sole pharmaceutical active principle, present at a concentration of at least 3% by weight, preferably ranging from 3 to 10% by weight, more preferably from 3 to 5% by weight and more preferably still of 5% by weight, with respect to the total weight of the composition.
  • Topical composition is understood to mean a composition intended to be applied to the skin and/or mucous membranes.
  • Physiologically acceptable medium is understood to mean a medium compatible with the skin, mucous membranes and/or superficial body growths.
  • a second subject-matter of the invention is the use of a topical composition comprising rucinol or one of its salts, as sole pharmaceutical active principle, at a concentration of at least 3% by weight, preferably at a concentration of 3 to 10% by weight, more preferably of 3 to 5% by weight and more preferably still of 5% by weight, with respect to the total weight of the composition, in the preparation of a medicament intended for the treatment of disorders of pigmentation of human skin.
  • a further subject-matter of the invention is a method for the dermatological treatment of skin pigmentation, comprising the administration of a composition according to the invention to an individual to be treated.
  • Rucinol is also known as lucinol or 4-(n-butyl)resorcinol.
  • Rucinol salts is understood to mean in particular salts formed with a pharmaceutically acceptable base, in particular an inorganic base, such as sodium hydroxide, potassium hydroxide and ammonia, or an organic base, such as lysine, arginine or N-methylglucamine, but also the salts formed with fatty amines, such as dioctylamine, aminomethyl propanol and stearylamine.
  • a pharmaceutically acceptable base in particular an inorganic base, such as sodium hydroxide, potassium hydroxide and ammonia, or an organic base, such as lysine, arginine or N-methylglucamine, but also the salts formed with fatty amines, such as dioctylamine, aminomethyl propanol and stearylamine.
  • rucinol will be used.
  • rucinol used as sole active agent, in a topical composition makes it possible to obtain an optimum depigmenting activity while retaining good tolerance of the composition by the skin and thus to limit side effects, such as irritation.
  • This activity is obtained when the rucinol is present on its own in the topical composition at between 3 and 10% by weight, with respect to the total weight of the composition, and preferably between 3 and 5% by weight and more preferably at 5% by weight, with respect to the total weight of the composition.
  • compositions comprising from 3 to 10% of rucinol, used as sole active agent, and preferably from 3 to 5% of rucinol make it possible to obtain much greater activities than the product comprising 4% of hydroquinone, the product conventionally used to treat hyperpigmentary disorders.
  • the product comprising 0.3% of rucinol already existing on the market shows an activity identical to that obtained with the reference product comprising hydroquinone, nothing presaged that the significant increase (at least 10 fold) in the concentration of rucinol in the composition would make it possible to obtain greater effectiveness with regard to hyperpigmentry disorders, such as melasma, while maintaining as good tolerance as the product sold at a lower concentration (0.3%).
  • the compositions according to the invention make it possible not only to be alternatives to the use of hydroquinone but, in addition, to obtain better results in terms of effectiveness.
  • topical compositions according to the invention thus make it possible to reduce local hyperpigmentation of the skin. Specifically, they produce a depigmentation of the skin area on which they are applied.
  • Depigmentation is understood to mean to obtain a decolouration of a hyperpigmented skin area until a colour is obtained similar or close to that of the neighbouring skin.
  • compositions of the invention are particularly well suited to the treatment of disorders of pigmentation, such as:
  • postinflammatory hyperpigmentation in particular due to infections, allergic reactions, mechanical injuries (such as an abrasion), reactions to medicaments (such as tetracycline, bleomycin, doxorubicin, 5-fluorouracil, busulfan, arsenic compounds, silver, gold, antimalarial medicaments, hormones and clofazimine), phototoxic eruptions, a scar, a trauma (such as a burn) and also the consequence of inflammatory skin diseases (such as acne, psoriasis, rosacea, lichen planus, lupus erythematosus, atopic dermatitis and cutaneous T cell lymphoma);
  • compositions according to the invention respectively comprise 3 and 5% of rucinol; they are compared with the composition comprising 0.3% of rucinol, a concentration conventionally used in cosmetic products, and also with the composition comprising 4% of hydroquinone (product Eldoquin Forte®).
  • the products were applied once daily, 5 days per week, for 12 weeks.
  • the clinical evaluation of the effectiveness of the product tested was carried out by the measurement of the brightness (L*) ( FIG. 1 ).
  • FIG. 1 represents the variations in L* measured each week, with respect to the measurement of L* obtained originally before the 1st application, for each product on the face of each patient.
  • the curve ( ⁇ as continuous line) represents the mean values of the variation in brightness obtained for the 16 patients with the composition comprising 5% of rucinol, compared with the composition comprising 0.3% of rucinol on the other cheek ( ⁇ as dots).
  • the curve ( ⁇ as continuous line) represents the mean values of the variation in brightness obtained for the 16 patients with the composition comprising 3% of rucinol, compared with the composition comprising 0.3% of rucinol on the other cheek ( ⁇ as dots).
  • the curve ( ⁇ as continuous line) represents the mean values of the variation in brightness obtained for the 16 patients with the composition comprising 4% of hydroquinone (product Eldoquin Forte), compared with the composition comprising 0.3% of rucinol on the other cheek ( ⁇ as dots).
  • This study shows a marked increase in the brightness with the compositions comprising 3 and 5% of rucinol in comparison with the compositions comprising 0.3% of rucinol or 4% of hydroquinone.
  • the three curves obtained with the three compositions comprising 0.3% of rucinol are virtually identical and are not significantly different from that obtained with the composition comprising 4% of hydroquinone.
  • This study demonstrates a better depigmenting activity on the part of the compositions according to the invention, compared with the composition comprising 0.3% of rucinol and also with the composition comprising 4% of hydroquinone. And, contrary to all expectations, this study also demonstrated that the compositions according to the invention tested are very well tolerated; specifically, the side effects are not significantly enhanced by the increase in the concentration of rucinol.
  • compositions of the invention can additionally comprise any additive conventionally used in the pharmaceutical and dermatological fields which is compatible with rucinol or its salts.
  • Topical route is understood to mean an application on the skin and/or mucous membranes.
  • compositions of the present invention can be provided in any formulation form normally used for a topical application, in particular in the liquid, pasty or solid form and more particularly in the form of ointments, of aqueous, aqueous/alcoholic or oily solutions, of dispersions of the lotion type, of aqueous, anhydrous or lipophilic gels, of powders, of impregnated pads, of syndets, of wipes, of sprays, of patches, of foams, of sticks, of shampoos, of compresses, of washing bases, of emulsions with a liquid or semiliquid consistency of the milk type, obtained by dispersion of a fatty phase in an aqueous phase (Oil in Water) or vice-versa (Water in Oil), or of suspensions or emulsions with a soft, semi-liquid or solid consistency of the cream, gel or salve type.
  • aqueous, aqueous/alcoholic or oily solutions of dispersions of the lotion type, of aqueous, anhydr
  • compositions by the topical route can be provided in the anhydrous form, in the aqueous form or in the form of an emulsion or also of microemulsions, of microcapsules, of microparticles or of vesicular dispersions of ionic and/or nonionic type.
  • the composition is provided in the form of a salve, of a cream, of a lotion or of a gel.
  • a depigmenting cream for the skin of oil-in-water emulsion type is prepared, which cream comprises (% by weight):
  • a depigmenting gel for the skin is prepared, which gel comprises (% by weight):

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Communicable Diseases (AREA)
  • Immunology (AREA)
  • Oncology (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US13/126,215 2008-10-28 2009-10-28 Depigmenting topical compositions and their uses Abandoned US20110274727A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/126,215 US20110274727A1 (en) 2008-10-28 2009-10-28 Depigmenting topical compositions and their uses

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US10906108P 2008-10-28 2008-10-28
FR0953745 2009-06-05
FR0953745A FR2946249B1 (fr) 2009-06-05 2009-06-05 Compositions topiques depigmentantes, et leurs utilisations.
PCT/EP2009/064238 WO2010049462A1 (en) 2008-10-28 2009-10-28 Depigmenting topical compositions and their uses
US13/126,215 US20110274727A1 (en) 2008-10-28 2009-10-28 Depigmenting topical compositions and their uses

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US20110274727A1 true US20110274727A1 (en) 2011-11-10

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US13/126,215 Abandoned US20110274727A1 (en) 2008-10-28 2009-10-28 Depigmenting topical compositions and their uses

Country Status (12)

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US (1) US20110274727A1 (es)
EP (1) EP2349192A1 (es)
JP (1) JP2012506851A (es)
KR (1) KR20110074890A (es)
CN (1) CN102196803A (es)
AR (1) AR074073A1 (es)
AU (1) AU2009309687A1 (es)
CA (1) CA2735887A1 (es)
FR (1) FR2946249B1 (es)
MX (1) MX2011003943A (es)
RU (1) RU2011121659A (es)
WO (1) WO2010049462A1 (es)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9801971B2 (en) 2009-10-09 2017-10-31 Beiersdorf Ag Transdermal therapeutic patches containing 4-N-butylresorcinol
WO2018150395A3 (en) * 2017-02-20 2018-10-25 HAKKI, Erkan 4-n-butylresorcinol preparations

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITLI20110006A1 (it) * 2011-07-04 2013-01-05 Ivo Pera Composizione per la cura della vitiligine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4959393A (en) * 1988-05-09 1990-09-25 Kuraray Company, Ltd. Skin depigmental agent

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6858217B2 (en) * 2002-03-22 2005-02-22 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Stabilization of terpenoids in cosmetic compositions
US6869598B2 (en) * 2002-03-22 2005-03-22 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Stabilization of sunscreens in cosmetic compositions
CN100496452C (zh) * 2003-12-15 2009-06-10 可乐丽股份有限公司 皮肤外用剂
JP2005179237A (ja) * 2003-12-18 2005-07-07 Kuraray Co Ltd 皮膚外用剤
JP2005179239A (ja) * 2003-12-18 2005-07-07 Kuraray Co Ltd 皮膚外用剤
JP2005179238A (ja) * 2003-12-18 2005-07-07 Kuraray Co Ltd 皮膚外用剤
JP5165860B2 (ja) * 2006-06-19 2013-03-21 株式会社クラレ ４−アルキルレゾルシノールを含有する皮膚外用剤
FR2931663B1 (fr) * 2008-05-30 2010-07-30 Galderma Res & Dev Nouvelles compositions depigmentantes anhydre comprenant un derive phenolique solubilise.
FR2931662B1 (fr) * 2008-05-30 2010-07-30 Galderma Res & Dev Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise.
JP2010030910A (ja) * 2008-07-25 2010-02-12 Kuraray Co Ltd 皮膚外用剤

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4959393A (en) * 1988-05-09 1990-09-25 Kuraray Company, Ltd. Skin depigmental agent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9801971B2 (en) 2009-10-09 2017-10-31 Beiersdorf Ag Transdermal therapeutic patches containing 4-N-butylresorcinol
WO2018150395A3 (en) * 2017-02-20 2018-10-25 HAKKI, Erkan 4-n-butylresorcinol preparations

Also Published As

Publication number Publication date
AR074073A1 (es) 2010-12-22
FR2946249A1 (fr) 2010-12-10
MX2011003943A (es) 2011-05-03
KR20110074890A (ko) 2011-07-04
CA2735887A1 (en) 2010-05-06
EP2349192A1 (en) 2011-08-03
FR2946249B1 (fr) 2012-07-06
WO2010049462A1 (en) 2010-05-06
JP2012506851A (ja) 2012-03-22
RU2011121659A (ru) 2012-12-10
AU2009309687A1 (en) 2010-05-06
CN102196803A (zh) 2011-09-21

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